The Career Development Discussion You Need to Have With Your Boss

Today’s employees need to OWN their own career development but many employees need the wisdom and guidance of their supervisor in order to achieve their career goals.

This is Part 2 of a 2-part series. In Part 1 we looked at career development discussions from the supervisor’s perspective. Today we look at career development discussions from the employee’s perspective.

Career development discussion: a discussion between someone and his or her supervisor, for the purpose of helping him or her develop to his or her optimal capability over time.

Career development discussions have recently become a rising star among best practices across all employment sectors for attracting, retaining, and developing talented people.

Yet many employees do not know where and how to start the process of having regular career development discussions with their supervisor.


Why Career Development Discussions?

How do employees feel about their supervisor holding regular career development discussions with them? Here are five typical comments I hear from employees whenever conduct an employee engagement study for a client:

1. The meetings tell me my boss cares about me and what I’m getting out of my employment, not just what my boss can get out of me.

2. My boss is interested in my future and wants to help me reach my goals.

3. I feel less engaged when I don’t have regular conversations about my career progress.

4. I’d like to have them more frequently, not just once a year at employee appraisal time.

5. When my boss takes a personal interest in me, it makes me want to work harder.

In other words, career development discussions say more about a supervisor’s / employer’s commitment to an employee than just about anything else. They are seen as an investment of quality time in the employee’s future.

Here’s another set of recent statistics and trends that make a compelling case for regular career development discussions with employees.



How to Have an Effective Career Development Discussion With Your Boss

As a rule of thumb, you OWN your own career development plan, while your manager should be to act as both your thinking partner and an accountability partner. Here are some steps to take to initiate and participate in regular career development discussions with your boss, if your boss hasn’t taken steps to invite you to participate.


Stage 1: Planning for the Discussion

  • Assess your own “career development performance” and determine where you are (developing, strong performer, or outstanding performer).
  • Identify an initial set of objectives for the short term (6-12 months) and longer term (2-5 years).
  • Develop a few questions you’d like to ask your manager, such as how he/she assesses your performance, what he/she sees as your strengths and weaknesses, and what you need to do to ready yourself for your next career step.
  • Ask your manager to meet with you to help you do some career planning in your current role with your current employer. Caveat: don’t make your request for a meeting sound like you are thinking of leaving!

Stage 2: Hold the Discussion

  • After asking your manager of where he or she sees you in your career development, share where you see yourself. If there are differences, use your time together to explore them.
  • Ask for his/her advice on helping you close any gaps in your skills or knowledge.
  • Identify an initial set of objectives you’d like achieve and ask your manager’s support.
  • Agree on the format of future discussions, such as how often you’ll meet, how much time for each meeting, and a shared agenda for each future discussion.
  • Schedule your next career development discussion with your boss.
  • Agree on what actions each of you will take between now and then.

Stage 3: Plan for Your Next Discussion

  • Thank your supervisor a few days after meeting in an email, and confirm in writing your deliverables for next meeting.
  • Fully deliver all commitments you made before the date you committed.
  • Reach out to your supervisor if needed, to answer questions, get spot guidance, and to update him/her on your progress.
  • Propose discussion items at least one week in advance of your next scheduled discussion.
  • Fully prepare for your next meeting the day before you meet.

Repeat Stages 2 and 3 and show your boss you OWN your own career development plan!


Bottom Line

Career development discussions are an employee best practice when the employee takes ownership of his or her own career development.

Author’s note: this article was in part excerpted from my Leading Through People series, LTP-17 Holding Effective Career Development Discussions.

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For the past 25 years I’ve worked with some of the world’s top employers by helping them get the most out of their talented people. My company’s extensive leadership development course catalog provides effective skills-building for everyone in the organization, from the new / developing leader to the seasoned C-level executive. My company’s coaching programs produce significant results in compressed periods of time. I also help job seekers, higher ed, and employment services connect people to better jobs faster. My company’s acclaimed career development tools help people navigate the ever-changing landscape of conducting a successful job search.  To find out more, please visit us at, email us at, or call us at 215-942-0982.


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